Winning Rory Back
by DensiNCIS
Summary: Tag to A Year In The Life Of. Jess looks through the window of the Gilmore girls and is so not over her.
1. Chapter 1

I walked out the door to leave Luke and his family to themselves. Luke followed me out to say goodbye and once again asked if I was over Rory. 'Why does he always ask me that?' I thought, but swiftly answered that yes, I was very much over her. I said a final goodbye to Luke and that I would see him tomorrow on his big day, but as Luke walked back in the house and closed the door, I walked over to the window and looked in. There she was, my beautiful Rory. Except she isn't mine. My face fell and I thought about how our journey has been so far. I could admit it wasn't the greatest love story, but I do still love this woman so very much.

After her visit to Truncheon Books so many years ago I was convinced that she would never be mine and we would never speak again. I figured I would see her on some family occasions, because Lorelai and Luke were together, but I could avoid her otherwise. My heart broke that day she came to Truncheon and I wasn't willing to let it all go just yet. And I did avoid her most of the time and only shared pleasantries with her on family occasions, but other than that I tried my best to let her go.

But everytime I am in the same room as her my heart will skip a beat and I catch myself checking if she has a ring on her finger yet. The day I heard from Luke that she did not accept _his_ proposal I was extremely happy. Even if I could not have her I still wanted her to be happy and I never thought she would be happy with that blonde dick.

But one day she walked into Truncheon once again and she had a very determined look on her face. She marched up to me and told me that we needed to talk. I simply nodded and led her upstairs to my office. I had once lived above Truncheon, but moved out and turned my old room into an office. She sat down in the armchair across from my desk and looked at me sternly. I chuckled and looked at her slightly amused. I was wondering what she would say, but was happy that she came to see me.

"We need to talk!" she said "Because I know you have been avoiding me the last 2 years and even at our family gatherings you hardly speak to me and just disappear to 'talk to Luke' or whatever."

"Rory... Look..."

"No Jess, no. I know that I hurt you 2 years ago when I came in here and kissed you and left again." Jess cringed at that. "And I know that you know that I am very sorry about that and also that I rejected Logan's proposal on my graduation day. So why haven't you and I had a normal, adult conversation yet? Do you seriously think you can keep avoiding me forever? Because let me tell you, I won't let that happen. Everything that happened will not be forgotten, but I think we should forgive eachother and move on from the past. I wonder how you are and I have to ask Luke while you are right there. That isn't fair Jess. You know how sorry I am. And I forgive you for everything that's happened since you came to Stars Hollow, but do you forgive me? I would like to be friends Jess, to just be able to talk to you once in a while and get updated on your life and share mine with you." _Her rants would never change_ he smiled.

"Rant over Gilmore? Good. Listen now. I have missed you like crazy and I would love to share my life with you, I just didn't know where we stood and if you wanted me in your life. I hate Logan and I didn't want you to feel caught in the middle. But I am sorry for avoiding you for so long and yes I do forgive you for everything that's happened. I want to be your friend and move on."

"Good."

"Yes, very. So... How are you?"

I'm smiling at the memory and look at her for a moment longer. I turn around and head over to Liz and TJ for the night. Oh how I wishes I could have stayed here with Rory. My beautiful Rory.

The last 8 years we have been talking a lot. Email, phone calls, visits. And I love that we can talk again and I am able to share my life with her. If only I could just win her back again... Damn. I'm a broken record. But I can't help it, she is the reason for me succeeding in life after all. She is intelligent, beautiful, decisive, stubborn and my best friend. She is always there and the girls I dated over the years just didn't hold a candle to his Rory.


	2. Chapter 2

The wedding is in the town square, which made to look like a fairyland. How very Lorelai. I bet Luke had absolutely no say in this, but I know now that he just loves her too much to argue about the simple stuff. I would do anything to have that with Rory. A do-over if you will. I treated her like crap when we were were growing up in this weird little town. I'm glad we're friends again, but I want to show her so much more of me. Today is gonna be difficult. I'm the best man, she is the maid of honor.

Once it's time for the ceremony she walks down the aisle and I can't help but stare at her. She looks so beautiful, it's torture not being able to hold her close and kiss her. Once she's standing in place opposite us men she looks at me and smiles. Oh that smile...

After the ceremony it's time for the first dance of the bride and groom. As everybody is invited onto the dance floor to join them I ask Rory if I can have this dance.

"Hey. Isn't it costumary for the maid of honor and best man to have a dance as well?"

Her face seems to light up at my question. "I would love to dance with you. I just figured you werent much of a dancer. You know, too cool and whatnot" she winks.

"Hey I'm not one to let a dance with a beautiful lady slide."

She grabs my hand in one of hers and places the other on my shoulder. It feels good to hold her even if just for one dance, but I try to keep my cool and just talk and laugh with her as we dance.

"Hey Jess?"

"Yeah?" I look at her expectantly.

"Thank you for this, I love to dance with you, but I know you're not a big fan."

"As I said, it's customary. I'm not one to dishonor traditions" I grin

She laughs and smacks my chest in laughter "You're ridiculous. You will never change will you?"

I'm starting to feel like a love struck little girl with all these thoughts running through my mind, but her saying that actually hurt. Because I have changed and I can only hope she knows that. I think my face fell at her words, because she says "Hey, I know you've changed. I didn't mean it like that."

"I know you know, Ror. I was just thinking about how far we've come since we were 17 years old" I try to hide.

"You've come a long way from the broody, moody James Dean type."

"And you have come a long way from this uptight, town-adoring little girl I met." I'm serious, she has come a long way, but it doesn't mean I didn't love her for who she was. Even back then I admired her.

"Hey!" She slaps my chest again "I was not uptight and I still adore this town." She actually pouts at me as she says this.

I laugh at her and in a sudden move I pull her closer to my body and put my hands on her waist. She stills and her hands are flailing now that she has nowhere to put them. Well she does, but I notice she is having doubts about this.

I smile at her and say "See, still uptight. You cannot even handle dancing with me."

I let her go and try to hide my disappointment at not being able to sweep her off her feet with my move. But before I have pulled back all the way she places her hands on my shoulders and looks at me with a warm smile.

"Oh I can handle dancing with you."


	3. Chapter 3

_A/N: Hey guys. Sorry it takes me so long to move on with the story. I will definitely finish it, but it may take some time. Please be patient :) Anyway, thank you for your reviews/follows/favorites so far, know that it's appreciated!_

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It felt so good to have Rory in my arms tonight. I'm sure the party is still going on, but I excused myself saying I needed to do some work. A lame excuse, I know, but I couldn't handle the closeness with Rory anymore.

After our dance we sat at a table drinking some champagne and just talking about anything and everything. I was studying her face and a smile formed on my face. I could just look at her all day every day. She is an incredible beauty. She looked so carefree tonight, just happy being at her mom and Luke's wedding, finally. We danced once more after a couple of drinks and this time she allowed me to pull her close to me. I think she's had a long day, combined with a couple of drinks, makes her kinda fall into me, unstable on her feet. I was enjoying holding her though, until she started complaining about guys. One guy in particular. _Him. Logan._ I just wanted to turn away right then and there, but I couldn't do that to her. She kept mumbling that he was going to marry his big dynastic plan, whatever that means. At some point I saw the tears pool in her eyes and it felt like a knife to my heart. This beautiful girl will never be mine, she will always choose him over me. That thought hurt me so much that I decided to bail out on this party. Rory looked kind of hurt that I was leaving her alone after her mumblings, but she smiled sadly at me and waved goodbye.

And now I'm lying on one of Liz and TJ's couches thinking about Rory and _him._ But the more I think about it, the angrier I become. I thought she broke it off with that douchebag and now here she is complaining about him marrying his dynastic plan? What the fuck is that about? Has she been seeing him again? Isn't she with Paul? Why won't she be with me? I love her, I always have. _God, I turned into a softy._ With all of these thoughts running through my head I fall into an uneasy sleep.

I wake up to my phone ringing. I check to see who it is and see it is Rory calling me. I definitely do _not_ want to talk to her, but if I ignore her she is gonna come digging. "Hey Ror, sleep well?'

"Goodmorning sunshine. Yes I slept well actually. How are you? Did you get your work done last night?" She asks me all chipper. I scowl at her on the other end of the line. How can she just skip over the fact that she was complaining about Logan while she was dancing with me?

"Yeah." I answer, back to my old clipped self. I know I should not be so short with her, but I'm hurt and she doesn't have a clue.

"Good. So I figure you have to get back to Truncheon soon? Do you want to do our traditional 'see you soon' lunch?"

Damn it. Lunch? It has become a tradition between us. We didn't want a goodbye lunch everytime we had to go, we always kept in contact and knew we would see eachother soon. So we made it our 'see you soon' lunch. But right now I would be okay not seeing her for some time. Unfortunately our friendship has grown so strong over the years that if I choose to ignore her now she will sense something is up. I know at some point I have to talk to her about last night, but the pain is too fresh. I can't believe the pile of mush she has changed me into. When I just came to town I couldn't care less about any of the people in this town. Until I met her. I wish I could just put my armor back on and run from here. But with Luke comes Lorelai and with Lorelai comes Rory. There is nowhere to hide. I decide to bite the bullet and just see how this is going to play out.

"Jess, are you still there?" I hear her question.

"Yeah. Okay, so let's have lunch. Luke's and then picknick at the bridge?" The bridge is our favorite place in Stars Hollow and it's usually quiet so I can think.

We are sitting on the bridge, our legs dangling of the side, eating our burgers and salt and peppered fries. It feels like old times and all of the sudden I feel sad looking at Rory and thinking about last night. Fortunately I got my pokerface on today and I can just smile and keep our everlasting dicussion on Ayn Rand, the political nut and Ernest Hemmningway, who has only lovely things to say about her, going. With that memory I actually feel a smile forming and we chat away for hours.


	4. Chapter 4

Just sitting here talking about books and the wedding is relaxing. I am enjoying hearing Rory talk about the new book she is reading and looking at the small smile that is always on her face when she talks about books. But I'm lost in thought again as I think about last night when she was a little tipsy and kept going on about Logan his big dynastic plan. It really hurt, but I also want to know more. WHY does she always choose that jerk over me? What does he have that I don't? Besides the rich family and a trust fund?

I decide to ask her, I need to know and she won't volunteer the information. "Hey Ror..."

She looks startled, being interrupted in her story, but looks me in the eye, conveying that I should talk.

"Last night, when we were dancing, you kept talking about Logan and his big dynastic plan. What was that all about?"

She casts her eyes down and sighs. I know she's turned him down in the past, but I also know she's still seeing him in their friends with benefits way. That fact alone is killing me, but I didn't want to push her away again so I didn't pass judgement on that. But she knows it's a touchy subject for me and tries to refrain talking about him. But this time I need to know what she was going on about. Is there a chance she is finally sick of him?

"I don't wanna talk about it", she mumbles.

"Ror, come on, tell me. I know you try not to speak about him on my behalf, but you kept going on about him and his big dynastic plan yesterday. I just want to know if I need to kick his ass to defend your honor", I say.

She giggles and says that that's not necessary. "I really don't want to talk about it Jess, please don't force me to."

I sigh and try one more time. "Are you still friends with benefits? And what is this dynastic plan? Is it about his work?" I sound like a girl trying to get all this information out of her, but with her I just can't help myself. And if he is hurting her, I want to know.

She sighs back at me and is silent for a minute, contemplating I think. She looks up again and says "Have I told you that he's engaged?"

I nod my head. That's the opinion I keep to myself... "Well, when he came to me a few weeks ago to take me out for the weekend with the guys, we had such a good time that I started wondering why he was still with Odette. So I asked him if he was really gonna marry her and in stead of answering me he said that it was the big dynastic plan. I just can't get him to tell me what it is that _he_ wants."

"What do you want him to want Rory?"

"Me." She says so quietly I don't think she wanted me to hear that.

"You want him? Even after you said no to his proposal? Even now that you are the other woman? Or do you want him to want you so you can keep f#cking him?" I'm really angry right now. She was in that moment last night, with me. I know we are good together and we have a great relationship nowadays. Why is she wasting her time on this jerk who apparently will just cheat on her in a heartbeat? Why can't she see what is right in front of her?

I see hurt flashing in her eyes and then she te up and starts to walk away while yelling at me about what a good friend I am being. I think that maybe I ought to be the sensible one right now and decide to go for the truth. I get up, run after her and grab her elbow. "Yes I am being a good friend. I've always kept my opinions to myself, but you are being naive right now Rory. He will not leave her just to be with you. And even if he would, he has already proven that fidelity means nothing to him. And I am a good friend for trying to get you to see that. But you are not a good friend Ror. We danced last night, we had a moment and you still can't see what's in front of you... ME, Rory, I am right here and I. Love. You." I'm so angry right now, I release her arm and storm off.

Oh shit... I've done it again...


	5. Chapter 5

I decide to go to Luke's and pack my stuff. I'm done with her right now and I just need to get my head on straight. This time the ball is definitely in her court... Although, I do want to know what she is thinking right now. I never gave her the chance to explain, to react. Damn it!

I still go to Luke's and pack up my stuff. Either way I have to get back to Philly tomorrow. Maybe she will come to her senses in the mean time, hopefully...

I've packed my dufflebag and throw it in the corner next to my bed. I check my phone but there are no missed calls or texts. A little dissapointed I walk down to the diner and help Luke. I really feel like going over to Rory and shaking her till she gets it, but enough is enough and she has to take the next step. I'm irritated though and stomp around the diner helping the people of Stars Hollow. Luke has learned to leave me be, but clears his throat at me after a while. Annoyed, because he is in the way of the coffeemaker, I look up and frown at him. He keeps silent and raising a brow points outside. Looking up I see Rory power walking in front of the entrance to the diner. Unwillingly my lips lift into a small smile, maybe more of a smirk, and I walk over to the entrance.

I open the door and just stand on the steps. She heard the bell above the door and jumping a little at the sound, she turns to face me. "Hi" she says quietly, not looking down.

I don't dare decipher her look right now. But I don't let her lash out, I've had enough and I am not in the wrong this time. Yeah, maybe I came down on her a little hard, but she needed it. And I need her. So I step up to her, grab her waist en pull her towards me. Smirking I say hi back and then I go in for a kiss. It all happens so quickly that she is a little slow to respond, either positive or negative, but after about a minute she sure does...


	6. Chapter 6

Hey guys, I'm sorry if you are getting a lot of updates right now. Doc manager is not cooperating on my phone unfortunately. Hope this will work now. Otherwise look out for an update tomorrow.

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She pushes me away and looks at me with wide eyes. "Jess!" she gasps. I don't think she is mad though, I think I genuinely shocked her.

"Rory?" I probe gently.

"But... I-I thought that... Uhh..."

"That I didn't see you that way anymore?"

She seems to have gotten herself together and looks up at me with a little smirk. What just happened? Why is she smirking like that?

"Well there's a reason I always tried to keep Blonde Dick out of our conversation." She laughs a little. "You are not that mysterious anymore Jess."

Now it's my time to look stunned. So she has always known? All this time? And never said anything? Well, that probably says enough, doesn't it. But I'm not showing my insecurities here, so I lift an eyebrow and say "Well, miss Gilmore, does that mean that you simply don't care about that fact and just want to be friends?" Yeah Jess, I silently admonish myself, that didn't sound insecure at all. Be a man. Do something.

But she just smiles and says "Now mr. Mariano, what do you think of me? I care about you very much. So much in fact that I tried to get a reaction out of you with my 'drunk talk' about..."

I growl and grab her by her waist en pull her towards me. One hand on her hip and the other cupping her face I pull her lips to mine and kiss her like we did when we were kids and I finally got the girl. I feel like a champion, finally having the girl of my dreams in my arms. And this time I'm not going to let her go.

I pull back and we smile at each other. "Is this what you wanted miss Gilmore? Me kissing you? Leaving you breathless and wanting more?"

"You sure are full of yourself!" She slaps my chest with a big smile on her face. "But yes, I'm finally where I ought to be, want to be... There's a reason I turned him down Jess and after we finally became close again I started to realise that it was actually always you. You stole my heart being your broody self."

I'm still holding her by the waist and lean in for another kiss. This angel is finally mine. "I'm not letting you go this time, you hear me?"

"That goes the same for you buster. You are not running away again when things get tough. You talk to me and we will get through it, together. I'm yours Jess, always and forever."


	7. Chapter 7

I know I should acknowledge what she just told me, that I should assure her that I'm not going anywhere this time. We will talk about whatever comes up between us, I will not run again. I know this is my last chance to be with the girl of my dreams and I'm going to do all that is necessary to keep her. But instead of telling her this I just grab her by the waist again, pull her against me and kiss her hard.

When my lips finally leave hers we are both breathless. Oh she looks so good right now, all flushed and beautiful. I can see the love shine in her eyes as she eyes me. She bites her lip and then leans her head on my shoulder. I hear her sigh contently and I just hold her.

After a moment I put one hand on her shoulder and make her look up at me by cupping her face with my other.

"Hi." I mumble, smiling wide.

"Hi." She giggles.

I decide to tell her again how much she means to me and start to ramble. "I know I can't run from you again, we will have to talk about all that arises. But I don't feel any need to run anymore, Ror. I don't ever want to loose you again. I love you Rory, I always have and always will."

She looks up at me again and smiles her sweet content smile. Oh I love seeing that smile. "I know Jess. All of it. I love you too." And with that she cuddles into my chest again and this time it's me that sighs contently. I kiss her on the top of her head and just revel in the feel of her in my arms again. This broken record is broken no more.

 _I've won Rory back._


End file.
